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Synthesis of novel non-natural conformationally restricted cyclopropane amino acids of spirane series

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Abstract

New conformationally rigid spirane analogues of γ-aminobutyric acid, namely, 4-aminospiro[2.2]pentanecarboxylic and 1-aminospiro[2.3]hexane-5-carboxylic acids were synthesized from the corresponding 4and 5-methoxycarbonyl-1-nitrospiro[2.n]alkane-1-carboxylic esters obtained in turn by the [1+2] cycloaddition of ethyl nitrodiazoacetate to methylidenecycloalkanecarboxylic esters.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, Department of Chemistry, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    N. V. Yashin, E. B. Averina, A. V. Chemagin, Yu. K. Grishin, T. S. Kuznetsova & N. S. Zefirov

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    N. V. Yashin, E. B. Averina & N. S. Zefirov

  3. LLC “Valentek”, Build. 2, 18 ul. Generala Dorokhova, 119530, Moscow, Russian Federation

    M. E. Zapolskii

Authors
  1. N. V. Yashin
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  2. E. B. Averina
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  3. A. V. Chemagin
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  4. M. E. Zapolskii
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  5. Yu. K. Grishin
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  6. T. S. Kuznetsova
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  7. N. S. Zefirov
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Corresponding author

Correspondence to E. B. Averina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2178–2181, September, 2015.

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Yashin, N.V., Averina, E.B., Chemagin, A.V. et al. Synthesis of novel non-natural conformationally restricted cyclopropane amino acids of spirane series. Russ Chem Bull 64, 2178–2181 (2015). https://doi.org/10.1007/s11172-015-1135-8

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  • DOI: https://doi.org/10.1007/s11172-015-1135-8

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